I personally have begun running all of my insurance past a local public adjuster here in the Chicago area that I met at a REIA.

I assume you have a security deposit?

@India Huguely Congratulations on making the first big step to pursuing your goals, making them public.

Yeah that makes sense on a larger property there are economies of scale so hiring security cost per unit wouldn't be as expensive. 

Is there a security deposit? 

We do have a secured solid wrought iron fence/gate to the alley, so the tenants are secure as long as they remember to lock the gate.I will go ahead and try to contact our council member and see if anything sticks there.

Your friend should send a demand letter for the return of his security deposit, or whatever portion of it he feels should be returned.

However, the work we have to do (we do the turnover most of the time), along with the aggravations that come with dealing with the general public have made it not worth it any more for us, and we'd like to convert it to a traditional SFR.

We do have simplisafe which might have failed to ring.My idea is to have a security guard who can be present at the property while no one is working there.

Roughly speaking, my mortgage payment would deflate (reducing my "rent payment") or if I rented it out the rent increases would inflate, keeping the previous numbers "real."4)  Social Security @ age 62, $1,760.The above scenario does not include my taxable account of  ~ 110K, which is about 15% stocks, 10% bonds, rest high yield savings cash.